A pinball of a man who constantly bounced from task to task, Sheppard was four weeks into a buyout after a three-and-a-half decade newspaper career.

He had helped break open one of the biggest college football scandals in history at Southern Methodist University. He had covered Super Bowls. He had served 21 years as sports editor through the golden age of Tampa Bay area sports.

Now he needed something to do.

“Somebody’s going to have to take a flyer,” he remembers thinking.

Sheppard, 59, had management and communication skills built through the newspaper career he fell into through a fluke at The Ohio State University when the prospective optometrist got crosswise with organic chemistry and then randomly was assigned to cover lacrosse for a journalism class. He fell in love with sports journalism.

After stints at papers in San Angelo and Dallas, Texas, he took a job covering the NFL for the St. Petersburg Times, soon moving into management and then becoming sports editor in 1993. The sports market was expanding rapidly, adding the NHL Tampa Bay Lightning, the major league Tampa Bay Rays and a Division I football program at the University of South Florida.

“We just got to do so much,” Sheppard said, noting a Tampa Bay Buccaneers Super Bowl title in 2003, Lightning Stanley Cup win in 2004 and Rays World Series appearance in 2008. “I used to brag to my colleagues around the country … that we were still able to think about what can we do that’s bigger and better and grander.”

But the challenging economics of the newspaper industry eventually caught up the the Times with tighter space, earlier deadlines and layoffs. “It started to dry up quickly,” Sheppard said. “The creative parts of the job were more challenging because everything was about money.”

By late 2014, the outlook at the paper, which had re-branded into the Tampa Bay Times in 2012, was bleak. Sheppard decided to jump and took a buyout. He had some advantages: His wife, Cindy, had a good job with strong benefits; they were financially stable; he had renovated his house.

“All the big-ticket things were behind us,” he said.

Sheppard had an interest in working with children that had been stoked in 2003 when he and Cindy mentored a boy through the Big Brothers Big Sisters program for four years. Knowing he could afford to make less and wanted to make a difference by working with youth, Sheppard focused on non-profit organizations that worked with kids. His connections through the Times helped him get in to visit with CEOs and other leaders of area organizations.

Getting his foot in the door helped Sheppard in many ways. He learned skills he hadn’t needed as a sports writer and editor, such as public speaking and PowerPoint presentations.

“It was scary to me. It was frightening,” he said. “I hadn’t done it, and I wasn’t very good at it. But I did it.”

After 35 years in the newspaper business, Sheppard said the learning experience was rejuvenating and transformative, teaching him he’s not too old to learn.

“What you really know how to do is think and organize and communicate …” he said. “The fact that these skills are transferable is very encouraging and even more so there’s so much new stuff I’m learning to do. It’s heartening.”

After about six months, Sheppard was promoted to managing director of marketing and partnership development. His experience recruiting “Bigs” helped him lead a revamp of the organization’s recruitment system that has streamlined the process and dramatically increased the yield rate and quality of candidates from applications.

“That’ll be my legacy …” he said. “That’s all any of us want to do. We want to have an impact. We want to use our brains and do something that works, that helps. And they’ve let me do that.”

Jack Sheppard’s tips for finding your Encore:

Use your connections: Find job prospects at Indeed.com or another service, but use your contacts to get in the door rather than depending on blindly sending a resume.

Get your foot in the door: Find an organization you’re interested in and be willing to take a lesser job to learn the skills and the organization. You can advance from there.

Look for your opportunity and knock on the door: Once you know the lay of the land, take initiative to seek a position that allows you to have greater impact.

I spend a good portion of my time everyday keeping up with new trends for older workers. One thing I’ve certainly noticed is that the job market has had its ups and down over the last twelve months. Despite these turbulent times, several recent articles in the New York Times and conversations with our favorite jobs expert, Kerry Hannon, have revealed a more optimistic outlook for older job seekers.

A recent New York Times article cited a new research report by the Center for Retirement Research at Boston College , which zeroed in on jobs where hiring is abundant for 50+ workers. The research found that a large number of these jobs, but not all, require lower skilled workers.

Kerry Hannon acknowledges the realities of ageism in the workforce but sees a brighter outlook by looking at other numbers and research reports. A new Brookings Institute Survey found that the largest growth in the labor force over the last seven years was amongst the population between the ages of 62-64. The U.S. Department of Labor also reported that the unemployment rate for older workers was lower than younger generations.

Employers need to find and engage older experienced workers and figure out ways to transfer knowledge to newer and younger leaders.

Job seekers need to adapt to the changing work landscape and be open to use their skills in other industries.

All of this is more great news for the 50+ job seekers!

After talking to hundreds of older job seekers, Kerry Hannon finds that although money is important, there are many other factors that are equally important, such as flexibility, sense of autonomy, benefits, and working for a company or nonprofit whose mission they believe in.

Don’t forget consulting and part time contract work as 42% of U.S. executives surveyed expect to use contract workers in the next two years.

Market your vast experience. Nothing is more important than real life experiences.

The outlook can be bright when we stay open and look beyond the traditional work paradigm. Another recent article highlighted a multitude of part time and gigs such as freelance and consulting, many of which are available and highly suited to older workers.

We are committed to building an even stronger network of organizations and individuals who can help you locate and upgrade your skills to find the right pathway to your encore! Every day we are finding more and more local companies that are specifically looking to hire older, experienced workers.

Other Pathways events in 2017 will connect you to valuable entrepreneur resources and an Encore Job Showcase.

Let me know if you are aware of other organizations and individuals who are committed to helping adults locate alternative jobs or pathways to purpose and income. I welcome other organizations who want to join our Encore Tampa Bay Network!

Last month we covered the topic of Ageism and how society’s view of getting older can create obstacles for those of us who are re-imagining a new stage of life. This month I would like to challenge all of us to stop looking at the perceptions and attitudes of those around us, but rather to look at aging from the inside out.

How can we turn those negative stereotypes and predictions into an incredible opportunity for change and growth?

The encore movement and longevity revolution has begun to outline the silver lining of putting our experience and talent to work in meaningful ways while enjoying these bonus decades of life. Boomers are the second largest generation with over 10,000 adults turning 65 every day. This means a WHOLE lot of us can truly reshape the norms, policies, practices and outlook for retirement, work and living in the second half of life! (and for generations to come).

So why is there so much concern about approaching this exciting new stage of life? Some of the comments or questions I continue to hear from folks in mid life:

How will I fill those bonus decades with meaning and purpose?

How can I stay healthy throughout this extra period of life?

How can I continue to earn income or to ensure long term financial security?

Joanne Jenkins, CEO of AARP, (one of my favorite heroes), and author of a national bestselling book, “Disrupt Aging” has done an outstanding job of showing us how to embrace the opportunities of aging and to address some of these internal concerns. “Disrupt Aging” focuses on three key areas: HEALTH, WEALTH AND SELF. Jenkins provides a wonderful narrative of her own journey along with many others who are working to change what it means to age in America and to truly enjoy this next stage of life. The book also provides great tips and programs that will assist us in each of these three areas.

Kerry Hannon, our recent keynote speaker (and another of my favorite heroes), spoke at our annual conference about the importance of having a three part Fitness Plan:

The survey showed that Boomers are beginning to take proactive steps to work past 65- starting with the top five steps:

Staying healthy so I can continue working.

Performing well at my current job.

Keeping my job skills up to date.

Networking and meeting new people.

Scoping out the employment market and other opportunities available.

In a more recent article by Joanne Jenkins, she talks about the “Four Freedoms of Aging” (taking it right from the playbook of Franklin Delano Roosevelt in 1941, during World War II), when he talked about the four freedoms: Freedom of speech, Freedom of worship, Freedom from Want and Freedom from Fear. Joanne challenges all of us to rethink our own beliefs and begin to spark new solutions on how to live and age in America!

Just like in 1941- we need to realize that WE have the freedom to choose the life we want to lead.

The Freedom to Choose – It is important for you to choose how you want to live your life in the second half; including improving your health!

Freedom to Earn – We CAN continue to earn income by re-imagining our work and breaking down the institutional and social barriers.

Freedom to Learn – Learning is critical to our success, whether it be keeping up with new advances in technology or upgrading our job skills or learning to be an entrepreneur.

Freedom to Pursue Happiness – This is all about discovering and fulfilling your purpose (the heart and soul of the Encore Movement!)

Encore Tampa Bay has decided to make these three important focus areas a major theme for the next 12 months. If we know that health, wealth and self are top of mind for those in mid life, then Encore Tampa Bay is committed to bringing resources and experts to help you answer and deal with these three areas.

We will be offering a series of different events such as:

“Health, Wealth and Self “speaker series.

Encore Pathways Showcases offering a variety of options for new pathways.

Encore Academy sessions that address health, wealth and self.

What are you waiting for? Let us acknowledge and embrace this positive side of aging!!

It is time to name the elephants in the room – age and experience!!

There is not a week that goes by that I don’t hear from job seekers about how frustrated, angry or simply dumbfounded they are by their inability to land a job that suits their experience! Hiring managers are saying over and over again they are overqualified for the job which is code word for they are too old.

The next time you see those two elephants dancing in the background of your interview, you can make one of two choices:

Buy into the assumptions, questions, and concerns of the hiring manager. OR

Be prepared for the elephants and change your own mindset and responses in that situation.

Chris Farrell, (author of “Unretirement”) offers great advice when confronted with the “overqualified” response in an interview. Acknowledge the concerns that the hiring manager has and reassure them you are working for a better work-life balance and not another rung on the career ladder.

John Tarnoff, a nationally recognized career reinvention coach, offers a few tips to minimize the great age divide between you and the younger hiring manager.

Do not shut down or over react when ageism rears its ugly head.

Do not lecture or give advice to the younger manager during the interview.

Avoid telling stories about how things were when you were their age.

Remember you

are not here to impress them with all of your years of experience, but to be of service and to contribute to the organization.

I have heard from so many of our workshop participants that hearing they are too old or too qualified starts playing into their own self-identify and mindset. This is your time to shine and point out all that you have to offer an organization or team of people!

Here are some additional strategies to strengthen your mindset/ attitude and address the elephants in the room:

Talk about your character strengths and “potential “. A service attitude, a long term vision, strong work ethic, curiosity, flexibility, engagement, willingness to try something new. Another great article by John Tarnoff.

Keep up with the times. Be familiar with changes in the field, new technology, use of social media and realities in the workplace. Refer to Kerry Hannon’s book, “Getting the Job You Want after 50”, a great resource for all job seekers!

Market your age and experience as a plus. Being experienced means you are resourceful, a good leader, great networker, team player, and political savvy.

Be clear in your own mind and with your interviewer why you want this job. Clearly state your motivations and expectations for taking this job at this time of your life.

Show a willingness to learn, try something new, and adapt to this new way of work!

Finding a job in 2016 is a whole new ballgame with new rules and new skills to stay competitive with the younger generations and tougher job market. It means learning different ways to search, network, and interview. Most important, it starts with YOU. Have faith in yourself and adopt the right mindset. Build a great support system to pull you back up whenever you see those elephants in the room!

Encore Tampa Bay:

There are plenty of upcoming Encore Academy sessions along with our other Encore Tampa Bay network of resources/organizations that are ready to support you in your job search. Go to our website under Encore Resources for all the upcoming events and programs!

It seems like everywhere you turn today – everyone is talking about finding true happiness or finding your true purpose or calling. An important key theme we hear in all of these areas is that it is an “INSIDE JOB”. It is not something that someone else can provide for you or a workshop that tells you the ten steps!

Why is it so easy for us to quickly identify what we DON’T want but when it comes to identifying what we do want, we get stopped in our tracks. I remember when I was in the beginning phase of this “WANDERING AND WONDERING “ chapter in my life and I was doing an Oprah self help quiz on finding your purpose…. and boy did I get stumped with the question – what do I really want? Why was that so hard for me??? This may be because we were all so busy in our lives doing what we knew HOW to do, or what people EXPECTED us to do or what we thought we SHOULD do.

After three years of talking to people in this mid-life stage of life, THIS question “What do I really want?” is the number one question or challenge that most people experience. Is this because we are stepping away from the comfort of who we have always been or what we have always done? Is it because we never thought we had the freedom to really ask that question – to have the freedom to really do what we wanted to do all of our lives? How do we get past these roadblocks to find what we really want- what is our purpose???

After reading many books, articles and connecting with others within the Encore Movement – here are my recommendations of how to get started:

Start on the INSIDE – It means stepping back and doing an internal search and reflection.

Test out or explore new opportunities and ideas – It is OK to fail, pivot, meander around to see what fits and what does not fit.

Stay focused on WHAT you want before you jump into the HOW and all the specific action steps to get there!

Marci Alboher, in her book, “The Encore Career Handbook” provides some valuable self-assessments that can help you get started with some of the internal reflection part of the journey. I would like to add a few more to the list from my own personal experience.

Keep track of your thoughts, ideas and internal brainstorming with a journal. Start with a crazy creative list of ideas you might have been kicking around for the last 30 years. Then make a list of all the things that you do not want!

Describe yourself, create a work/life snapshot. In our “What’s Next” workshop we have people draw a circle of life; what they are currently doing in all areas of their lives- and then draw an ideal, future circle.

Examine your motivations. Do you want to earn a lot of money, do you want to work with a team of people, do you want to address a community issue? (more of these questions are in the Encore Career Handbook)

Talk to your closest friends. Ask them what your greatest strengths are? What are the things people always come to you for help with? What skills do you enjoy doing??

Describe some of the issues that draw you in or people you want to serve? What are your top five values at this time in your life?

What are some of the roles that appeal to you (not the ones you have been stuck in for the last 30 years).

What are the skills you WANT to use or that you want to learn how to do?

PUTTING IT ALL TOGETHER:

Once you have done some of that internal reflection and assessment, you will want to step back and look at any themes or clues that can give you enough to get started on your next step which is ACTION AND EXPLORATION.

Connect with other like minded people who are in this same stage of career transition. (Meet ups, discussion groups, workshops to learn something new– or start your own little accountability group)

Network with people who are doing interesting things perhaps in areas that you want to learn more about. (You are not asking for a job, you are asking others to talk about themselves or their job; this is exploring 101.)

Find a volunteer opportunity in an area that sounds interesting for you. Research shows that volunteering can be your best way to learn about yourself and what fits for you. Volunteering can also be a way to test drive some of the values or missions that you want to align with. Volunteering is the best way to secure a job or a short term consulting project in a non profit organization.

I would encourage any of you who are at the beginning of this “wondering and wandering” phase to purchase the Encore Career Handbook because it takes you beyond the finding your encore phase to help you examine all the different pathways you can go!

ENCORE TAMPA BAY CAN BE A RESOURCE FOR YOU..

PATHWAYS AND RESOURCES TO HELP YOU DISCOVER, RETOOL AND CONNECT:

The Encore Academy continues to offer free discussion groups that are centered around topics that assist people with making career transitions or finding your purpose. Our website also connects you to other great organizations and resources that will assist you to discover, retool and connect to what ever your encore might be!

CONNECTING TALENT TO THE COMMUNITY

We are ready to help get you plugged into the needs and opportunities of the non profit community with our new non profit opportunity board or listings of other websites and matching programs where you can use your skills to strengthen a non profit in our community!!

IT IS TIME TO GO DO A LITTLE DIGGING AND EXPLORING!

Encore Tampa Bay is an initiative of the Community Foundation of Tampa Bay, a registered 501 (c ) (3) organizations. Donations accepted by the Community Foundation to support the work of Encore Tampa Bay are tax deductible.